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Copper‐Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon‐Carbon Bonds of 1, 1‐Disubstituted Alkenes with Sulfonyl Hydrazides
Author(s) -
Yi Dong,
He Linying,
Qi Zhongyu,
Zhang Zhijie,
Li Mengshun,
Lu Ji,
Wei Jun,
Du Xi,
Fu Qiang,
Wei Siping
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000549
Subject(s) - chemistry , alkoxy group , regioselectivity , bond cleavage , cleavage (geology) , alkyl , sulfonyl , catalysis , carbon fibers , ionic bonding , medicinal chemistry , carbon–carbon bond , reinforced carbon–carbon , combinatorial chemistry , stereochemistry , photochemistry , organic chemistry , ion , materials science , geotechnical engineering , fracture (geology) , composite number , engineering , composite material
Main observation and conclusion Alkoxy radical‐mediated carbon‐carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic‐type transformations. However, carbon‐carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon‐carbon bond for the oxysulfonylation of 1,1‐disubstituted alkenes, providing facile access to a variety of valuable β‐keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β‐scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.